| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5268667 | Tetrahedron Letters | 2010 | 5 Pages |
Abstract
The l-proline organocatalytic homodimerization of 2-cyclohexenone has been studied and it is concluded that the mechanism of the reaction follows competing pathways involving either a two-step imine/enamine addition or a concerted Diels-Alder cycloaddition where the ultimate product distribution is dependent upon the ratio of the organocatalyst to 2-cyclohexenone and a base present.
Graphical abstractAn organocatalytic homodimerization reaction is shown to proceed via a cascade mechanism involving enamine-iminium ion intermediates in competition with a concerted Diels-Alder pathway.Download full-size image
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Vanina Guidi, Sergio Sandoval, Michael A. McGregor, William Rosen,